🌟 The 5 lessons that have guided my career
Or: when reflecting on the key choices of my life so far, the five first principles that have emerged.
Last week I was invited to my daughters' school to speak to the high schoolers for Career Day.
Talking to 15-18 year olds about a career is a fascinating experience - now seen both through the lens of my 12 yo who will soon be there, but also vividly remembering those years for myself as a kid in Vancouver.
I took them through the chronology of my life - from the sciences to brand management to my MBA to consulting to China to babies to venture backed tech startups to now, AI.
The point was not to suggest the specifics of my life as any kind of roadmap, but rather give a guidebook of the lessons that they might apply to theirs.
They boiled down to these 5 first principles:
1. 🔵 Dots not ladders. I was a really great ladder-climber. I had to be, to go from the my family's modest immigrant background, to some of the most amazing company and educational opportunities. And I had to build my own safety net along the way before I could really start taking leaps. So I focused on companies and education that allowed me to leap into successively new categories of future opportunities and backstop further leaps. But once I had a sufficient safety net, I realized that further ladder climbing was not going to serve my life. Instead, I started to focus on "dots”.
My favorite Steve Job’s quote says: “You can only connect the dots looking backwards". I stopped obsessing over the next rung of the ladder - this Director role or that project and started focusing on the dots that might serve me. Moving to Shanghai was the start of the approach - taking a massive leap that we believed would be a life experience no matter what, still supported by the safety net of a big company. Choosing dots over ladders became increasingly easier after that.
2. 📈 Choose the "dot" that maximizes the slope of your learning curve. How do you know if a “dot” is the one to pursue? Forever a student of science, I don’t think in terms of absolute values, but the rate of a thing. I’ve always focused less on the specific milestones and accomplishments to gather but rather on maximizing the steepness of the learning. Ironically, this approach usually ends up getting to the milestones and accomplishments but not because I aimed for it. It’s the approach that had me knowing nothing of brand management but saying yes to P&G in Toronto at 21, nothing nothing about the US but saying yes to Cincinnati at 24, all the way to knowing little about tech or AI originally, but saying yes to YC and OpenAI most recently.
The only decisions I re-litigate in my mind are the times I didn’t follow this rule for myself- the times I took the safer or seemingly "sexier" path. Each time I regretted it but found my way to quickly jump back. There was a period after graduating from my MBA where it seemed like I couldn’t stay at a place longer than 2 years. Turns out it wasn’t bc of my ability to commit, but my inability to find a sustainable place where my learning curve stayed steep.
When you have the option, choose thing (or the person) that will teach you the most in the shortest amount of time. That might be at a big company or a small. It might be across the world or in your backyard. The specifics matter way less than people make them out to be. Focus on the learning. Then if you stay for 6 months (the minimum I think for anything new, but more on that in minute) or 6 years.
3. 📆 The 6-month rule. If you're going to take leaps on the things that maximize your learning, then it's going to feel scary and sometimes you're going to get it wrong. So how do you deal with that? With something my first manager and mentor taught me as I considered the momentous decision of taking an international assignment in Geneva or Cincinnati. 23-year old me thought Switzerland was a no brainer. Jeff wasn’t so sure. He said, "Go learn how to run a US business and compete at that level - then any door will be open to you. And don’t take my word for it. Try it for 6 months. If it's not the thing you want, I'll personally pull you back and send you to Geneva."
That was (and remains) the most powerful thing someone could do for me- to not only honor my ambition and give me a big opportunity with a nudge, but a create a built-in safety net to make it feel safe and doable, especially so early in my career.
The 6 month rule words like this: Doing anything new feels scary. Add in something really hard and you're going to second guess yourself inside of the first couple of weeks. The natural reaction is going to be that you made the wrong decision and to quit. But the 6 month rule says you have to commit to 6 months of doing your all. Throw yourself into the full experience without reconsidering or waffling. Then at the 6 month (or even 12 months if you can) you can take stock and assess how its going. Most times you'll have gotten over the hardest bits and be excited about all the new that lies before you. But there will be times when you realize you've learned a lot and its actually shed light on the thing you're more interested in doing. And so you choose that.
In any case, this is a map for progress made of big leaps, made safe with practical safety nets.
4. 🤔 Learn how to think, not what to think. Anytime I get to speak to high schoolers or undergrads, I'll get the question - “what do you think I should study?”. I personally think it's the wrong questions to be asking, especially in our quickly evolving world. I rather think we need to focus on learning how to think not what to think.
Choose the thing that develops robust and complete mental models from which to evaluate the world. And if you can, choose multiple schools of thought - the sciences are fantastic to teach you about first principles and hypotheses or choose economics to learn about markets or psychology to learn about biases or philosophy or…. And then go travel. Go live in another culture and learn a completely new language. That will teach you more than an entire major might.
And finally, learn to be a lifelong learner - picking up more mental modals and testing them against the data of the world as you come across it. It’s the only way I know we’ll all be able to “compete” and keep up in this quickly changing world.
5. 👯♀️ Focus on the people not ideas. The other most common question I'll get is: “how do you get your startup ideas?” Again I think that's the wrong question to be asking.
This is also the one thing I wished I had been told or had learned earlier in my career:
In the early years, my job was not to focus on ideas but rather to collect two things - insights and people. The living and the learning from the previous point will lead to the ideas. But then you'll need the people to make it a reality. And truth be told - this is actually the harder part. When it comes time to work on something big and ambitious - who will be beside you? So as early as you can, start noticing who are not only the most intimidatingly talented people around you, but all the most fun to work with (for you). Start finding ways to work with them and test that out in practice.
The idea is to always have a shortlist of people you'd call up if you ever decide to do something - and by then it wont be a theoretical test, but a continuation of previous collaborations. And on the other side, you wont be a totally unknown quantity to them. That friend will know you and what you’re capable of.
There is so much more that I could probably impart but these are the 5 that I think are the most relevant and actually useful, especially for folks earlier in their career (or for anyone restarting in a new space).
Focus on the dots that maximize learning - commit to at least 6 months in gathering insights, mental models and amazing people.
The rest is trusting and living life in all in messy wonder.